


Me and you and you and me

by carameldumpling



Category: Gossip Girl, Supernatural
Genre: Alternate Universe, Crossover, F/M, Loss of Virginity, Sexual Content, Virginity
Language: English
Status: Completed
Published: 2011-04-24
Updated: 2011-04-24
Packaged: 2017-10-18 15:09:49
Rating: Mature
Warnings: Underage
Chapters: 1
Words: 3,398
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/190171
Author URL: https://archiveofourown.org/users/carameldumpling/pseuds/carameldumpling
Summary: <blockquote class="userstuff">
              <p>“I could follow you,” Serena reasons, the plan forming beautifully in her head like a well-thought drama series.</p>
            </blockquote>





	Me and you and you and me

**Author's Note:**

> Posted on LJ - 4 Oct 2009. Underage in the sense that Serena is 16 in this fic.

**2007**

The first time she sees him, it’s at the Met steps. 

Serena is eating a cupcake with blue icing, giggling at something Blair says about Chuck, when a sleek black muscle car comes around the corner. Muscle cars aren’t common around the Upper East Side, you see more limos than something like this. 

Blair nudges her. “Check out the driver.”

Serena squints, and the driver in question turns. She gets an eyeful of startling green eyes, high cheekbones and gorgeous lips. When he catches her staring, she does a double take, focusing again on her cupcake.

“I don’t think he’s from around here,” Blair’s still staring at the back of the car, enthralled. “He’s hot.”

“Yeah,” Serena licks her lips, wondering why she’s so flushed. “He sure is.”

  
Mr. Hot McSexass – as Blair christened the driver one day, drunk as a skunk and high on passive weed smoking – is forgotten until Kati’s parents throw their annual party at the Palace, and surprise surprise, he’s there, sipping champagne and looking like 15 kinds of fuckable in a suit.

“Oh god,” Blair murmurs, gripping onto Serena’s wrist like a lifeline. She adjusts the bosom of her Dolce and Gabbana strapless. “I want to fuck him.”

Serena raises an eyebrow at that. “What about Nate?” 

Blair has, after all, claimed the heir to the Archibald wealth as hers since they were five, convinced that they were both meant to be. Serena would like to think otherwise, because a couple of days ago Nate was clearly eager to go beyond second base with  _her_ , but they’re her best friends. And she would never hurt Blair that way, ever. 

“One night wouldn’t hurt.”

Serena shakes her head, grabbing a drink from a passing waiter and winking at him so that he’d keep quiet about the underage drinking she’s going to do tonight. Mr. Hot McSexass is screwing up her mind, and she’d like to think straight tonight, thank you very much.

  
Three cocktails, two tequila shots and one hard whiskey later, Serena’s leaning against the bar, squashing her boobs together to give the impression of cleavage to attract the bartender. 

It works.

“A Purple Nurple,” she declares, slightly tipsy, but managing to give the bartender a seductive smile. 

“Make it two,” a smooth voice says behind her, and she turns to see Mr. Hot McSexass. 

Oh god, he’s even more beautiful up close.

“It’s on me,” he murmurs, eyes trailing downwards to her boobs, but immediately flickering up again, and they were so green, even greener than Nate’s. 

“Got a name, sweetheart?” he asks, leaning against the bar, and all she wants to do now is to drag him into the toilet and beg him to take her virginity. Serena shakes her head, trying to clear it. No sex, she thinks firmly. No sex until you find the one you want. 

Well, technically that would be Nate, but he’s taken, isn’t he?

“Serena,” she manages, smiling carefree and happy, not the seductive grimace she gave the bartender minutes ago. “You got a name?”  _So I can stop calling you Mr. Hot McSexass?_

The bartender comes with two Purple Nurples, and Mr. Hot McSexass nods in thanks. “Dean.” 

He passes her the drink, before lifting his and clinking their glasses together. Serena downs her in a swallow, and she’s thrilled to notice that he does the same.

After all, not many boys on the Upper East Side go nuts on fruity drinks, preferring to show off with hard liquor, only to get ridiculous hangovers the next day.

“Want another, Dean?” she asks. “It’s on me.”

She sees the heat in his eyes when she says that, and she’s instantly convinced she’ll lose her virginity tonight. To Mr. Hot McSexass. Uh, Dean.

“What do you recommend?”

“Sex on the beach,” Serena replies instantly, eager to continue this flirtation.

Dean chuckles, loosening his tie a little. “I’d like that,” he says softly.

  
A couple of Sex on The Beaches, Cosmos, and a Screwdriver later, Serena is convinced she has found her dream man in Dean… Dean.

“You’re not from here, are you?” She’s holding her Jimmy Choos in one hand, walking barefoot in the Palace’s garden. He’s next to her, tie tucked in his pocket and shirt slightly untucked, and ridiculously hot. She’s so turned on she can’t think in proper sentences.

Dean laughs softly at that, but it lacks mirth. “No, I’m definitely not, Serena.”

She can’t get enough of how he says her name, as if it’s the most wonderful thing on earth. How unfair is it that the man she’s sure will make her happy for the rest of her life is going to leave soon?

“Fuck me,” she suddenly blurts out, and he looks up at her, alarmed. 

“What?” he asks, shaken, and Serena wonders if she’s read the signs wrongly. But she shouldn’t have. She’s Serena van der Woodsen. Reading signs is what she does best, next to mixing alcoholic drinks and eating cupcakes. And annoying Nate Archibald. Lovingly, of course. 

“Fuck me,” she repeats, staring at him expectantly. “I know you want to.”

Dean stares at her back, hesitant, before pulling her into one of the best kisses she’s ever had. She wouldn’t mind being stuck like this forever. It’s fantastic, and when he licks the inside of her mouth, she tastes the remains of his Screwdriver, and a hint of something that she thinks is pure Dean. 

She grabs his shirt, trying her best to unbutton it in her drunken state, and he pushes her back, gently but firmly holding onto her wrists. 

“What’s wrong?” 

Dean laughs again. “I cannot believe I’m going to do this.” He mutters to himself, letting her wrists go. “How old are you, sweetheart?”

Serena’s heart sinks. “Old enough.”

Dean steps forward, tucking her hair behind her ear. “You’re drunk, Serena. You don’t know what you want.”

That’s not true. “I do,” she grabs his belt buckle, pulling him in and makes a circle with her hips. He groans, closing his eyes. Serena can feel him hardening under his black slacks, and she needs to count to five before she loses it and attacks him like a wild boar. Or whatever animal that attacks people ferociously and passionately. 

“And you want it too,” she whispers.

Dean sighs. “Baby,” he says softly into her ear, making her shudder. He takes the opportunity to pull her hands away from his belt. “Baby, when you’re sober, and you still want this, you tell me.”

And then he’s gone, and Serena feels a little like a slut.

  
She doesn’t see him for the whole weekend, and Serena is sure that he’s gone, appalled by her behaviour. But Blair calls her on Sunday night, squealing about how she saw Mr. Hot McSexass near Tiffany’s when she went out with Nate that afternoon. 

“He smiled at me, Serena!” her best friend gushes. “I am in love.”

Serena feels slightly miffed. “You have Nate.”

“That’s long term, Serena. Like a safety net.”

Serena doesn’t know how to respond to that, only thinks about how Nate yanked her by the waist, high on pot, whispering to her,  _“It’s always you, Serena. Blair can never have my heart, just you.”_

And then she thinks of Dean and his dancing green eyes, and flops onto the bed.

  
He’s leaning against the muscle car a couple of blocks from her house on Monday afternoon after school, and she grins, walking up to him.

“Serena,” he smiles, and it’s almost brighter than the sun. She’s never thought of herself as a cheesy person, but around Dean this happens. 

“Dean,” she greets him, before looking at his car. “This yours?”

Dean nods, stroking the black car as if caressing a lover. “’67 Impala. My baby, seen me through a lot.”

Serena cannot believe she is jealous of a car. “She’s gorgeous,” she admits. 

At least she’s fighting for his affections with a hot car.

He looks at her then, really looks at her, as if trying to find out if she’s for real. Apparently convinced with what he sees, he nods. “Wanna go on a ride?”

“Okay.”

Dean grins, stepping up to her and giving her a kiss.

  
She spends hours after school with him, dragging him to her favourite places and some. They sit in Central Park, kissing until her lips feel sore and his are slightly swollen, food lying forgotten on the picnic mat she stole from the kitchen. He’s bored at the Met museum, and she understands his pain – she only brought him there because she thought tourists want to go to the Met, but Dean’s grinning when she suggests that they get out of there. She ends up at the back of Met, between Dean and the wall, moaning into his kisses and smirks. 

Dean dresses like nothing she’s ever seen, torn jeans and layers as if it’s cold, and a leather jacket that makes him look more gorgeous than usual. He holds her hand when they walk down the streets, plays footsie with her when they eat at the café near St. Jude’s, and actually walks on the outer part of the sidewalk, as if protecting her from the cars. It’s a dream come true.

They talk about everything and anything under the sun. Serena’s amazed by the number of places Dean has been to, and wishes she can say more than just The Hamptons and her grandparents’ villa up in Paris. But he’s eager to know how Paris is like, listening to her with wide green eyes that she can’t get enough of. He talks of cheap motels, blushing slightly as if embarrassed, but she smiles as wide as she can and asks where’s the nearest one, because she wants to visit it someday. 

Serena learns about his family – Dad’s busy but he’s always there when needed, Sammy’s a whining little bitch but an awesome brother, Mom died when he was four but he loves her still. They have a family business. Hunting, he admitted after she prodded him repeatedly. She doesn’t understand why he’s so reluctant to talk about the family business. She’s told him everything she knows – which is not a lot – about her family shipping business. 

Sometimes, though, Dean asks weird things, like whether anyone died in a building they walk past, any ghost stories she’s heard of, or any weird things happening. Serena thinks it’s part of his charm, something that makes him Dean. For the first time in years she eagerly goes to the school library in search of local folklore, surprising Dean when she waves papers in his face. She also surprises her teachers and the librarian, but whatever. 

  
Two weeks later, he’s waiting for her at the same spot, but he’s frowning. Dean doesn’t talk a lot, and Serena has to fill in the gaps of silence with what she did today in school, which bores even her. Math is not something she can make sound interesting, however hard she tries.

“I have to go,” he says finally, staring at his coffee.

Serena closes her eyes. The fairytale was going to end anyway.

  
She calls her mother, tells her that she’ll be staying over at Nate’s. Then she calls Nate, telling him that she’s going clubbing,  _please lie to Mom for me, Natie,_  and he relents, but informs her that she owes him big.

“You don’t hang out with us anymore, Serena,” he says, and she can see him pouting already. “I miss you. A lot.”

She’s forgotten her friends since Dean came, but it never really mattered, somehow.

Dean drives them to the nearest cheap motel after much persuasion on her part. He was reluctant at first because he was leaving, and then he found out she was sixteen and flat out said no. 

“Dean, please.”

“Oh god,” he had sound slightly strangled. “You’re underage.”

Serena had the sudden urge to punch something, but she just holds his hand, entwining their fingers together. “Please,” she whispered, looking at the calloused fingers and the rough edges. No one on the Upper East Side had calloused hands unless they were butlers, maids or had some service-related job. It was different from Nate’s well-moisturized hands and Chuck’s manicured fingers, but it was a good kind of different. It made Dean seem human and real.

He had looked at her with what she had dubbed his ‘assessing face’ before sighing and shifting gears. 

They now sit on the king sized bed. He explains to her that he was on a job, was supposed to finish it and go back, but she came along and he couldn’t resist. 

Serena doesn’t blame Dean, never did. He looks so distressed she feels hurt already, and that cannot do. She reels him in, kissing hard, and pulls him down on top of her.

Dean breaks the kiss, staring at her with the green eyes she’s grown to love. “You sure, Serena?”

She takes a deep breath, nods and kisses him again.

  
Dean’s gentle with her, as if she’d break if he touched her too hard. Serena doesn’t care about gentle, she just wants to feel. She holds on tightly onto his biceps as he strokes her clit, keening when he leans down to blow over it. When he latches onto her nipple, sucking it, teeth grazing lightly, she spasms, gasping as comes. 

He lifts his head up and looks at her, head tilted. “You’re a virgin, aren’t you?” he asks, voice raw, and she nods. He closes his eyes, as if it’s painful, and moans. 

“Oh god, Serena,” he ruts at her thigh once, before moving up to kiss her hard. She moans in delight, wrapping her arms around his neck and her legs around his waist, her hips tilting up automatically and grinding into him, making them both groan at the friction. 

“Fuck me, Dean,” she whispers wantonly into his ear as he nibbles on her neck. “Want it to be you.”

He pauses, taking a breath and raises his head, green eyes full of lust. “Don’t say such things unless you want this to be over real soon,” he grunts.

She giggles, and he smiles back at her, playfully rubbing his stubble on her neck. She squeals, trying to get away, but he’s on top of her and she can’t escape. The playfulness soon becomes something else when Dean rubs his stubble on her breasts, her navel – he dips his tongue into her bellybutton and she cries out softly, arching upwards – and down her bikini line. 

  
Dean makes her come twice with his rough fingers, once with his tongue – and that was an amazing, life-changing experience, in Serena’s opinion – and makes sure she’s pliant and relaxed before he hovers over her and slides in, biting her shoulder gently to take her mind off the pain.

She wriggles a little, the feeling of him inside her odd and full. He’s holding back, staying in place as she adjusts, sweat beading on his forehead. She wants him to let go, ram into her and make her howl, but he pushes away her hair from her face, kissing her face with a reverence that scares her.

“Your first time has to be awesome,” he says, one hand trailing her curves and landing on her clit. She arches against him, needing to be closer. 

“We’ll do the rough sex thing next time, okay beautiful?”

Oh god, he wants a next time. Serena cannot be happier, and she mewls happily, wrapping her legs tighter around his waist.

When he finally moves, she’s almost crying in pleasure. Every thrust says  _‘love you’_  and  _‘mine’_  and  _‘only you’_. She moves her hips in a rhythm that accompanies his, each wiggle saying  _‘yours'_ ,  _‘love you’_  and  _‘just you’_.

  
She wakes up in the morning slightly disoriented and wondering if she got drunk enough to break into someone’s house. Then she remembers the night before, and blushes. It’s a little sore down there, despite Dean’s good intentions and best efforts to make it not hurt as much as possible. 

Serena’s in an embrace, large arms around her waist. She turns and sees Dean, sleeping and unguarded. He’s even more beautiful then, the worry lines she sometimes sees on his face gone, eyes closed and lips slightly slack. The sun shines behind him, and it frames him, making him look unearthly, almost like one of those angels her father talked about when she was little.

As she traces the contours of his face, she thinks about how he would have thrived here. The Upper East Side was full of gorgeous people, and he could have been one of them, drinking expensive champagne in an expensive suit, smelling of expensive cologne. But instead, Dean drinks beer from the bottle, his jacket is his Dad’s and he smells of something she’s never quite smelt before, but she likes it anyway.

Serena’s so lost in her thoughts she doesn’t notice he’s awake. “Winchester.”

Okay, she has no idea what he just said. Wait, isn’t that the name of a gun?

“My last name. Winchester.”

He blinks, green eyes still groggy with sleep and pulls her closer to him. He looks like a small boy and it takes a lot of effort not to squeal and pinch his cheeks. Serena smiles winningly, running a hand through his hair.

“Dean Winchester,” she says, and likes it. 

  
The Impala stops a few blocks before her house. Serena doesn’t want to leave it. She’s fallen in love with the car, despite initial hatred, and it feels more like home than her huge house ever did.

“You should go.”

She turns to Dean, who’s trying hard to look nonchalant and failing. “I could go with you.”

The last time he looked so shocked was when they first met and she asked him to fuck her while she was almost batshit drunk. “What?”

“I could follow you,” Serena reasons, the plan forming beautifully in her head like a well-thought drama series. “I could help you with your family business. I’m sure I can get along with Sammy. And we could be together.” 

She’s never been much help, but she’s determined to make this work. If it means stealing Daddy’s accountant’s calculator and a graph book or two, she would. And surely cooking isn’t that difficult, right? 

Dean looks at her wistfully, and shakes his head. “You have no idea what you’re suggesting Serena. And you’re sixteen. I’m not gonna whisk away a minor and risk becoming a cradle-robber.” 

He leans over, and she inhales that smell that is Dean. His green eyes are intense, and slightly pained. “This is your life. Here, with the parties and the expensive stores. Not a long road.”

“You never know until you try.”

Dean bites his lip, staring at hers, before moving towards her.

The kiss is desperate and painful, tongues twining and Serena’s grabbing at Dean’s jacket for dear life, but the need for oxygen wins the need to never let go. When they part, Dean looks extremely determined to make sure she enters that house sometime soon. 

“When will I see you again?” she asks, because he has to come back. He can’t just leave her here for dead.

Dean sighs, rubbing the back of his neck. “When I have time, I promise I’ll come down. In fact,” he rummages the compartment that houses his Metallica tapes. “If you need anything, here’s my number.”

His handwriting is bold and neat, and she falls in love with it immediately, pretty much like how she had fallen in love with the person. 

“Come back soon?” she pleads, and he nods, tucking her hair behind her ear.

Serena nods and gets out of the car, walking to her house. The Impala is about to drive away when she runs back.

“Serena?”

“I love you.” She says. “I love you.”

Dean hesitates, fear and wariness in his eyes, and she thinks she’d said it too soon. Maybe he didn’t even feel that way. But then he smiles, and it’s like the sun is shining. “I love you.”

  
She hears, rather than sees, the Impala drive away, and she curls into a ball on her huge poster bed, wishing for the king sized bed in the motel. Serena clutches the paper with Dean’s handphone number and cries.

Falling in love shouldn’t be this painful.


End file.
